US3507953A - Pesticidal dithiophosphonic acid esters - Google Patents
Pesticidal dithiophosphonic acid esters Download PDFInfo
- Publication number
- US3507953A US3507953A US17500A US3507953DA US3507953A US 3507953 A US3507953 A US 3507953A US 17500 A US17500 A US 17500A US 3507953D A US3507953D A US 3507953DA US 3507953 A US3507953 A US 3507953A
- Authority
- US
- United States
- Prior art keywords
- stands
- grams
- ester
- solutions
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- FLQUDUCNBDGCRI-UHFFFAOYSA-N hydroxy-sulfanyl-sulfidophosphanium Chemical class SP(S)=O FLQUDUCNBDGCRI-UHFFFAOYSA-N 0.000 title claims description 4
- 230000000361 pesticidal effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 22
- -1 alkyl radicals Chemical class 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 230000001988 toxicity Effects 0.000 description 8
- 231100000419 toxicity Toxicity 0.000 description 8
- 241001124076 Aphididae Species 0.000 description 7
- 241001454295 Tetranychidae Species 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000009885 systemic effect Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
Definitions
- the present invention relates to and has as its objects new and useful insecticidal derivatives of dithiophosphonic acids and processes for their production.
- the new compounds of the present invention may be shown by the following formula:
- R and R stand for lower alkyl radicals, and R stands for alkyl radicals substituted by halogen atoms, cyano groups, organic or inorganic acyl groups or optionally substituted aryl groups.
- R stands for alkyl radicals substituted by halogen atoms, cyano groups, organic or inorganic acyl groups or optionally substituted aryl groups.
- the aforesaid substituents may also be linked to the alkyl group R via hetero atoms.
- dithiophosphonic acid esters are known already as pest control agents, part of them being important for practical purposes.
- alkylmercapto-alkyl esters of thioor dithiophosphonic acids are described in US. Patent No. 2,881,201..
- the new group of derivatives of dithiophosphonic acid which are also distinguished by an outstanding and partially systemic insecticidal activity, is obtainable according to this invention in a manner known in principle, i.e./e.g. by reacting the corresponding salts of O-alkyl-dithiophosphonic acids with correspondingly substituted alkyl halides.
- R stands for lower aliphatic or cyclo-aliphatic radicals up to 6 carbon atoms
- R more specifically should be a lower alkyl radical up to 4 carbon atoms and R may be a lower alkyl radical up to 4 carbon atoms, possibly interrupted by hetero-atoms such as oxygen, sulfur or nitrogen and furthermore substituted by halogen atoms such as chlorine and bromine, the cyano group, aryl radicals, especially phenyl radicals, possibly substituted 'by e.g. halogen atoms, lower alkylor aryl-, especially phenylcarbonyl groups, wherein the phenyl radicals also may bear substituents such as lower alkyl radicals or halogen atoms.
- R also may be substituted by another s OR l S-radrcal wherein R and R have the same significance as said above.
- the new compounds are excellent pest control agents and are intended to mainly be used for the protection of plants. They may be used in the same manner as other known phosphoric insecticides, i.e. in a concentration from about 0.00001% to about 1%, diluted or extended with suitable solid or liquid carriers or diluents. Examples of such solid carriers are talc, chalk, bentonite, clay and the 3,507,953 Patented Apr. 21, 1970 CzHr s-om-oo-Q (II) s 0on1.
- EXAMPLE 2 ozrno s s/ SCHzOCHa-S CzHs 84 grams /s mol) of ethyl-thionophosphonic acid-O- ethyl ester thiolphosphonic acid potassium salt are dissolved in 200 cc. of acetonitrile. 23 grams mol) of a,ot'-dichloro-dimethyl ether are added at 60 C. with stirring. The temperature is kept at 60 C. for a further hour and the reaction product is subsequently poured into 300 cc. of ice-water. The separated oil is taken up in benzene, washed neutral with water and dried.
- EXAMPLE 3 52 grams (0.25 mol) of ethyl-thionophosphonic acid- O-ethyl ester thiolic acid potassium salt are dissolved in 100 cc. of acetonitrile. 39 grams of w-chloro-acetophenone dissolved in 50 cc. of acetonitrile, are added at 40 C. with stirring. The temperature is kept at 40 C. for a further hour and the product is then worked up as described in Example 2. 66 grams of the new ester are thus obtained in the form of a pale yellow, water-insoluble oil which is not distillable even in a high vacuum. Yield 92% of the thoretical.
- Aphids are killed completely with 0.01% solutions.
- Larvae are killed completely with 0.00001% solutions.
- Alk in each case being alkylene of at least 1 carbon atom, the total number of carbon atoms in Alk 1d R'. being 4.
- Rn S-Alk-CN wherein R stands for alkyl having up to 6 carbon atoms, R stands for alkyl having up to 4 carbon atoms, and Alk stands for lower alkylene having up to 4 carbon atoms.
- R stands for alkyl having up to 6 carbon atoms
- R stands for lower alkyl having up to 4 carbon atoms
- R" stands for phenyl
- R stands for alkyl having up to 4 carbon atoms and R" stands for lower alkyl.
- R stands foralkyl having up to 6 carbon atoms
- R stands for alkyl having up to 4 carbon atoms
- R" stands for phenyl
- R stands for alkyl having up to 6 carbon atoms
- R stands for alkyl having up to 4 carbon atoms
- X stands for a member selected from the group consisting of oxygen and sulfur.
- R stands for lower alkyl containing 1 to 5 carbon atoms
- R stands for lower alkyl containing 1 to 4 carbon atoms
- A stands for alkylene containing 1 to 4 carbon atoms.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28059A DE1138047B (de) | 1959-03-28 | 1959-03-28 | Verfahren zur Herstellung von Dithiophosphonsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3507953A true US3507953A (en) | 1970-04-21 |
Family
ID=7092724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US17500A Expired - Lifetime US3507953A (en) | 1959-03-28 | 1960-03-25 | Pesticidal dithiophosphonic acid esters |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3507953A (fi) |
| BE (1) | BE589121A (fi) |
| CH (1) | CH393322A (fi) |
| DE (1) | DE1138047B (fi) |
| GB (1) | GB898313A (fi) |
| NL (4) | NL6807950A (fi) |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2494284A (en) * | 1949-01-12 | 1950-01-10 | American Cyanamid Co | Cyanoalkyl phosphates and method of preparation |
| US2494283A (en) * | 1948-02-04 | 1950-01-10 | American Cyanamid Co | Carbamylalkyl phosphates and method of preparation |
| US2611728A (en) * | 1949-11-01 | 1952-09-23 | Standard Oil Dev Co | Insecticidal compositions containing substituted aliphatic esters of diethyl dithiophosphoric acid |
| US2862017A (en) * | 1955-05-03 | 1958-11-25 | Bayer Ag | Benzyl esters of thiophosphoric acids and their production |
| US2881201A (en) * | 1954-12-04 | 1959-04-07 | Bayer Ag | Substituted mercaptoalkyl esters of phosphoric acids and their derivatives |
| US2884354A (en) * | 1955-08-30 | 1959-04-28 | Hercules Powder Co Ltd | Dithiophosphate insecticides |
| US2884353A (en) * | 1955-08-30 | 1959-04-28 | Hercules Powder Co Ltd | Dithiophosphate insecticides |
| US2908605A (en) * | 1955-11-03 | 1959-10-13 | Ciba Ltd | New organic phosphorus compounds and process for their manufacture |
| US2967884A (en) * | 1958-04-01 | 1961-01-10 | Union Carbide Corp | Preparation of acrylic acid esters |
| US3013047A (en) * | 1959-03-28 | 1961-12-12 | Bayer Ag | Phosphorus-containing derivatives of benzylmercaptan and process for their production |
| US3100735A (en) * | 1961-11-07 | 1963-08-13 | Stauffer Chemical Co | Bisorganophosphorus esters and their preparation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1014105B (de) * | 1955-09-07 | 1957-08-22 | Bayer Ag | Verfahren zur Herstellung von O,O-Dialkyl-thiophosphorsaeuretriestern |
-
0
- NL NL249895D patent/NL249895A/xx unknown
- BE BE589121D patent/BE589121A/xx unknown
- NL NL125459D patent/NL125459C/xx active
- NL NL137850D patent/NL137850C/xx active
-
1959
- 1959-03-28 DE DEF28059A patent/DE1138047B/de active Pending
-
1960
- 1960-03-22 CH CH320860A patent/CH393322A/de unknown
- 1960-03-25 US US17500A patent/US3507953A/en not_active Expired - Lifetime
- 1960-03-28 GB GB10945/60A patent/GB898313A/en not_active Expired
-
1968
- 1968-06-06 NL NL6807950A patent/NL6807950A/xx unknown
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2494283A (en) * | 1948-02-04 | 1950-01-10 | American Cyanamid Co | Carbamylalkyl phosphates and method of preparation |
| US2494284A (en) * | 1949-01-12 | 1950-01-10 | American Cyanamid Co | Cyanoalkyl phosphates and method of preparation |
| US2611728A (en) * | 1949-11-01 | 1952-09-23 | Standard Oil Dev Co | Insecticidal compositions containing substituted aliphatic esters of diethyl dithiophosphoric acid |
| US2881201A (en) * | 1954-12-04 | 1959-04-07 | Bayer Ag | Substituted mercaptoalkyl esters of phosphoric acids and their derivatives |
| US2862017A (en) * | 1955-05-03 | 1958-11-25 | Bayer Ag | Benzyl esters of thiophosphoric acids and their production |
| US2884354A (en) * | 1955-08-30 | 1959-04-28 | Hercules Powder Co Ltd | Dithiophosphate insecticides |
| US2884353A (en) * | 1955-08-30 | 1959-04-28 | Hercules Powder Co Ltd | Dithiophosphate insecticides |
| US2908605A (en) * | 1955-11-03 | 1959-10-13 | Ciba Ltd | New organic phosphorus compounds and process for their manufacture |
| US2967884A (en) * | 1958-04-01 | 1961-01-10 | Union Carbide Corp | Preparation of acrylic acid esters |
| US3013047A (en) * | 1959-03-28 | 1961-12-12 | Bayer Ag | Phosphorus-containing derivatives of benzylmercaptan and process for their production |
| US3100735A (en) * | 1961-11-07 | 1963-08-13 | Stauffer Chemical Co | Bisorganophosphorus esters and their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1138047B (de) | 1962-10-18 |
| NL125459C (fi) | |
| NL6807950A (fi) | 1968-08-26 |
| CH393322A (de) | 1965-06-15 |
| NL249895A (fi) | |
| GB898313A (en) | 1962-06-06 |
| BE589121A (fi) | |
| NL137850C (fi) |
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